1,2-Dichloroethane → HCID 68830156, compound

HRID 1784425Notes

Reaction equation

HRID 1784425 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:14]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=2)(=[O:17])=[O:16])=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[Cl:47]CCCl>ClCCl>[ClH:47].[CH3:2][O:3][C:4]1[C:14]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=2)(=[O:17])=[O:16])=[CH:13][C:7]2[CH2:8][CH2:9][N:10]([CH3:31])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68829698HCID 68829698, compound

Product 1

HCID 68830156HCID 68830156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of E1 hydrochloride salt (0.2 g, 0.5 mmol), sodium triacetoxyborohydride (400 MG), aqueous formaldehyde (0.5 mL, 37%), and 1,2-dichloroethane (10 mL containing 0.5 mL triethylamine) was stirred for 18 h then diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium hydrogen carbonate (100 mL), dried (MgSO4), and evaporated to give the title compound E2 isolated as the hydrochloride salt from ether (0.3 g). MH+ 423. 1H NMR δ (CDCl3) 2.39 (3H, s), 2.60 (4H, m), 2.97 (4H, m), 3.70 (3H, s), 6.65 (1H, s), 6.99 (2H, d), 7.20 (2H, m), 7.38 (3H, m), 7.63 (2H, m), 7.81 (1H, s).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate (100 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-bd6c72de39f6491b9953327da01f3109
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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